


Someone to Watch Over Me

by Saucery



Category: Teen Wolf (TV)
Genre: 1920s, Age Difference, Alternate Universe, Alternate Universe - 1920s, Alternate Universe - Historical, Alternate Universe - Mob, Alternate Universe - Non-Magical, Canon-Typical Violence, Class Differences, Class Issues, Coming of Age, Crimes & Criminals, Drama, Falling In Love, Guns, Happy Ending, Hurt/Comfort, Implied Child Labor, Italian Mafia, Life-Saving, Love, M/M, Newspapers, No Werewolves, Opposites Attract, Organized Crime, Orphanage, Orphans, Poverty, Prohibition, Reform, Reunions, Romance, Seduction, Serious Injuries, Snark, Sparks Fly
Language: English
Status: Completed
Published: 2013-05-01
Updated: 2013-05-01
Packaged: 2017-12-10 02:35:12
Rating: Teen And Up Audiences
Warnings: Underage
Chapters: 1
Words: 4,245
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/780777
Author URL: https://archiveofourown.org/users/Saucery/pseuds/Saucery
Summary: <blockquote class="userstuff">
              <p>Derek is a broody mafioso. Stiles is a gutsy newsboy. They fall in love.</p>
            </blockquote>





	Someone to Watch Over Me

**Author's Note:**

> The title is based on [this song](http://en.wikipedia.org/wiki/Someone_to_Watch_Over_Me_\(song\)) written by George and Ira Gershwin in 1926.

* * *

 

Damn. Stiles’s suspenders are so worn out, they look more like strips of ragged seaweed than items of clothing. The brass buckles are a dull, scratched brown and are more broken than not, but it’s not like he can afford to get new ones.

“Got any spares?” he asks Scott, but Scott’s got his nose buried in the pin-up of a wavy-haired brunette in a striped bathing suit. Scott’s tastes are very specific.

“Man, you know I ain’t got nothin’,” Scott replies, distractedly, thumb moving restlessly along his thigh.

Stiles snorts. “What you’ve got is a stiffy the size of Lady Liberty. I’m outta here.” He jumps off his bunk and heads for the door. “See you later.”

“The Ritz?”

“The Ritz.”

Not that Stiles is gonna be _at_ the Ritz; he’ll just be selling newspapers _outside_ of it, watching the swishy gentlefolk waltzing in and out, laughter bubbling out of them like champagne.

He settles his cap on his head, collects his papers from Mr. Harris down the block, and jogs to his usual spot, hoping that none of the other hulking street-boys have gotten there, first.

They haven’t.

Of course they haven’t; few of them are as desperate for money as Stiles is, especially since Stiles doesn’t do pick-pocketing on the side. It’s way too early for thieves, hoods and crooks to be skulking around.

The sun’s barely out, and a few carriages trundle half-heartedly through the sleepy grey mist of dawn. Even the lights of the Ritz are muted in the chilly fog, glowing eerily from across the street, like the round, golden eyes of some sea-beast from the deep.

There are a few people milling about, though, stern-mouthed businessmen with collars turned up against the wind and the occasional baker trundling out his stall, so there’re still customers to sell newspapers to.

Stiles takes up position under his favorite lamppost and starts calling out the news of the day. The papers slung across his arms waft with the scent of still-fresh ink.

Hopefully, he’ll sell a hundred by sundown, when he’ll go and get the late prints, and sell about a fifty of those. At 2 cents a paper, that oughta make him a whole $2.50 by nighttime, although he’ll lose most of that to Mr. Harris, the goddamn profiteer. Stiles will get at most 30 cents to keep for himself, when all is said and done.

He’s never going to save enough for new suspenders, is he?

*

Stiles doesn’t actually feel down about being an orphan, most days. Most days, he doesn’t think about it. Not-thinking is sort of a survival skill, around here.

Sometimes, he sees a grizzly, middle-aged cop doing his rounds and feels this _tremor_ run through him, a tremor that has his hands clenching on the newspapers he’s trying to sell, crinkling them, ruining a perfect batch.

Other times, he remembers the day he was told he’d lost his dad. Lost him to a shootout with the Italian mafia, to a couple of alcohol-smuggling schmucks during a fucking raid. And all because those Sicilian vultures wanted to make money off the prohibition, because some greedy assholes thought a hefty profit was worth more than a human life. The life of a cop. A father. A widower. A serious, devoted man, that could still laugh at himself for wearing an apron, for fumbling the pancakes he made for his son.

But mostly, Stiles doesn’t think about it.

He and his friend, Scott, are both orphans. Scott’s mom was a nurse, before the flu of 1918 took her. Scott doesn’t think much about that, either. Then again, Scott doesn’t think about anything. At all. But given how he keeps smiling that goofy smile of his, maybe he’s the wiser one.

They live in Dr. Deaton’s Home for Boys, a small but unusually well-run orphanage funded by Dr. Deaton’s astonishingly lucrative veterinarian practice. (Stiles still can’t get over the fact that some of the doctor’s clients include the pets of senators and the horses of visiting British _royalty_ , for god’s sake.) But Deaton’s a simple guy, unlike those snooty types - no pretensions about him, sleeves perpetually rolled up. Stiles knows he’s damn lucky it’s Deaton’s shelter that took him in, rather than one of the carnivorous workhouses that take in kids and spit out bones.

Or whores.

That said, it ain’t like Stiles doesn’t worry about what the hell he’ll do once he _has_ to leave the orphanage. He’s just turned seventeen. He’ll have to move out when he’s eighteen. But where to? He can’t pay the fees for any college, even though he’s smart enough to get into one. (He used to have this _massive_ crush on Lydia Martin, the town’s princess, who is as beautiful as she is brilliant - but he’d realized long ago that she was way out of his league. If only… No. It’ll never happen. She’ll end up in Harvard, and he’ll be sweeping the streets.)

Jackson - another guy Stiles’s age - grew up at the orphanage, too. But he’s been adopted by this glitzy lawyer and has since become an arrogant bastard that won’t even drop by to visit. He’s too busy pretending to belong among the hobnobbing rich folk, turning up his already upturned nose at everyone, wearing the snazziest clothes, hanging out with the wealthiest friends, betting on the fastest horses, dating the prettiest girls.

Lydia.

Dating _Lydia_.

What makes it sadder is that Jackson doesn’t even genuinely seem to care about her. Stiles occasionally catches them going out, Lydia in a lovely dress with a fur stole around her slender neck, and Jackson’s arm around her waist as he smirks that infuriating, I-own-everything-including-you smirk.

Damn him. Stiles can’t believe that once upon a time, he’d thought Jackson was cute, and had crushed on him as much as on Lydia. Maybe Stiles’s got a thing for people that won’t look at him twice. And why should they? All Stiles has to his credit are a couple of coins left over from his newspaper business, and top grades at the local school. But who cares about his grades? It’s not like he has a future. Orphans never do.

So, Stiles is considering various options - joining the military with Scott, maybe? - when he runs into Derek Hale.

Mafioso Derek Hale.

From the Irish mafia.

Whose wicked face is all-too-familiar to Stiles from the front pages of the very newspapers he sells.

The clean-up man, they call him. (The guy who keeps the city clean… of everyone but himself.) The vicious dog. The peace-maker. The widow-maker. The chivalrous killer. The silent brute. And on and on. There’re so many contradictory portrayals of the man that Stiles plays it safe by believing the worst.

Expecting the worst never hurts.

Or, heh. It hurts less.

Derek dresses like the best, though. Even if he is the worst.

He’s dressed in a sharp suit and silk trousers that probably cost more than what Stiles will make selling papers for the rest of his life, but he’s such a sour, broody sonovabitch that he might as well be living in a jail-cell, instead of in whatever palatial mansion he _does_ live in. He’s only in his twenties, but he’s got the gravitas of a forty-something veteran of war.

Oh, and he carries a gun. A very big… gun. Of, um, big. Proportions.

Trouble is, Derek doesn’t run into Stiles just once. He does it again and again. Derek’s taken up temporary residence in the Ritz, for shady purposes known only to him, and he buys the paper from Stiles, every evening, like clockwork. And glowers down at Stiles while doing it, like Stiles’s dumb peasant face somehow offends him.

That’s the effect Stiles assumes he has on Derek, anyway, until one day, he’s offered an unexpected deal.

“You’re Stiles, right?”

Stiles startles. Jesus, that voice is like a thundercloud. It even roils, and everything. “Yeah,” Stiles answers, cautiously. “How’d you know?”

“Heard you talkin’ to that other kid.”

Oh. Scott. Still, what does that have to do with -

“You look like you need some dough,” Derek says, his hat shadowing his face.

“Huh?” Stiles gapes up at him.

“If you deliver somethin’ for us, you’ll be rewarded. Richly rewarded. We need a new face for this, see, someone the cops won’t recognize.”

And Stiles just - _explodes_ , slamming the paper into Derek’s chest hard enough to actually make the man stagger a bit.

Derek looks stunned. Well, as much as a man with a shadowed face and a stubbled jaw can look stunned.

“Why, thank you ever so much for taking pity on my poverty, Mr. Hale, but it’s a decent poverty, and at least I didn’t have to sell my soul to get it. My hands ain’t stained with blood. And I’ll never do anything that might hurt cops, seeing as how my dad used to _be_ one. Got it? Now back off.”

Derek grits his teeth. “It was a swell deal.”

Stiles barks out a laugh that isn’t remotely like a laugh. “Yeah, that’s what the devil always says. Get outta here.”

And maybe Stiles is stupid. Maybe he’ll be dead before the night is up, shot full of holes in some alley on the way back to the orphanage. Maybe he’s offended the wrong man. No, he’s _definitely_ offended the wrong man. He’s just rejected Derek Hale, prince of the Irish mafia, nephew of Peter Hale, the Alpha of that particular pack of rabid wolves. Heck, forget the night, Stiles might not survive the next second.

But Derek just… pauses. All over. Something undefinable seems to come over him, and he just _looks_ at Stiles, like he’s never seen him before.

One of his gloved hands comes up - Stiles doesn’t flinch away from it, because he won’t, he’ll never flinch from a scumbag like this - and cups Stiles’s face, angles it into the streetlight, so that it shines into Stiles’s eyes, nearly blinding him.

Stiles is being studied. His entire face is being studied, and his - his _mouth_ , and Stiles doesn’t know what to _do_ with that, a hot, uneasy prickle running over his skin, making it break out in goosebumps.

He tries to blink past the light to see Derek’s eyes, but they just glint from under the brim of that hat, like an animal’s, avid and hungry.

Stiles clenches his jaw against the sudden (and suddenly _bizarre_ ) temptation to part his lips.

Derek’s gloved thumb ghosts over Stiles’s throat, a whisper of cool leather. Stiles shivers.

And Derek steps back.

“You’re a strong one,” Derek murmurs, and then he’s gone.

Stiles stares after him. And collapses against the lamp-post, knees oddly weak, legs reduced to jelly. He’s shaking. Shaking like a _leaf_. And maybe it’s just the shock of nearly getting killed, but -

It hadn’t felt like ‘nearly getting killed’.

It had felt like something else.

Something that makes Stiles touch himself, later that night, and hate himself for doing it, but doing it, nonetheless. Something that makes him bite his threadbare pillow so that Scott can’t hear him from the neighboring bunk. Something that makes him push helplessly into his fist and swallow his ragged moan.

Damn.

He has no idea how to face Derek, after this.

How to -

Does Derek even _want_ -

Because it seemed like -

No. It doesn’t matter. Stiles doesn’t want him _back_. Derek’s a gangster, for chrissakes. He’s on the wrong side of the law. And, okay, the Irish mafia is a darn sight more honorable than the Italians, in this town, and they’ve been known to protect the innocent, even being cast as heroes, or some such nonsense - but Stiles is certain that the ‘innocent’ are only those that pay for protection. They must be. Otherwise -

Otherwise, being in the mafia wouldn’t be such a lucrative business, now, would it?

*

So Stiles goes back to selling papers, and Derek - surprise, surprise - still insists on buying them from him. And pausing while doing it, just like he had the last time, and brushing his fingers against Stiles’s when he takes the paper, slipping them under Stiles’s wrist-cuff. Touching his skin.

It makes Stiles’s pulse jolt and his face heat, but he refuses to look away from Derek’s eyes, because he isn’t _afraid_ , that isn’t what this is about. That isn’t why he’s saying no. He’s saying no because it’s the right thing to do.

That, and Derek hasn’t outright asked him out on a date, or anything. Although Stiles isn’t even sure how that would work. Having dinner at a fancy restaurant with a wealthy mafioso, with Stiles dressed in his dirt-stained best? Yeah, right.

Stop. Just -

Stiles has to stop these thoughts. Right now.

And he’s on the verge of stopping them, one night - he really, really is - when the gun-shots go off.

Just behind the hotel.

In a darkened side-street.

And Stiles - being Stiles - runs toward the gun-shots, not away. For a few furious minutes, it’s like he’s a salmon, swimming upstream, fighting against the flood of people pouring out of the hotel and away from the scene. He keeps hearing the gun-shots in his head, although he knows they’ve stopped. His mind is an empty, boiling space. An echo-chamber. His ribs ache, like he’s been punched.

By the time Stiles gets there, Derek’s crumpled on the moonlit cobblestones, clutching his chest through his finely-tailored suit, his blood a black, gleaming river pooling between the cracks in the paving.

There’s nobody else around.

Where the heck are Derek’s bodyguards? Henchmen? Minions? Those two tall guys - Stiles vaguely remembers the names ‘Isaac’ and ‘Boyd,’ from the goons always following Derek around - or even that blond, black-coated girl that seems like she can kill people with her _nails_?

Where are they?

“Gone,” Derek rumbles, when Stiles asks him, frantically tugging Derek’s suit off of him and using it to staunch the bleeding. “I sent them away.”

“Why in the seven hells did you send them _away_?”

Derek just smiles. A frightening, toothy smile, and -

Nah. That crap won’t work on Stiles.

He sighs. Hauls Derek up and staggers with him to the main street, where folks either scram or instinctively shy away from the guy trailing a broad stripe of blood across the ground. Such outstanding examples of public conscience. Such concerned citizens. Jesus Christ.

Stiles keeps an eye out for anyone that might seem hostile, any remnant from the shootout, anyone resembling a marksman. (What does a marksman even look like?) But he can’t spot anything out of the ordinary.

“Put - put me down,” Derek growls. “ _Go_.”

“What, you want me to leave, too? Listen, jackass, I’m not an idiot. I read the papers. I _sell_ them, if you hadn’t noticed. I know there’s a war on. That you’re going after the Italians, and they’re going after you. Now, you may have sent your little brood away, to protect them - ”

“I didn’t - ”

“Shut up, sour-face.  I’m just sayin’. You might’ve sent them away, but I’m not yours to command, all right?”

“You never are,” Derek says, eventually, hoarse and soft and strange, and -

And Stiles has to get him to Dr. Deaton.

He _has_ to, so he does - hailing a cab and paying the cabbie everything he’s earned for the whole month, just to take them the four blocks to Deaton’s shelter.

“I’m not taking you to a hospital,” Stiles says, numbly amazed that he isn’t stuttering, like he sometimes does when he’s nervous. He’s never sounded so firm. “Don’t worry.”

“I… yeah,” Derek says, vaguely, pale and clammy, on the brink of passing out. “Yeah.”

Shit.

As it turns out, Dr. Deaton _can_ save Derek’s life, because Derek’s bandaged and stitched-up and recuperating, a few hours later, unconscious after being drugged full of morphine. He looks relaxed for the first time since Stiles has known him, his seemingly permanent frown smoothed out, his fists unclenched, his chest rising and falling slowly. Like he’s safe. At long last. Like he’s -

He _is_ safe. Nothing can happen to him, here. No one’s gonna expect a fucking mafioso to be hiding out in an orphanage on the poor side of town.

Dr. Deaton’s fixed him up just fine. The bullet hadn’t hit any vitals, thank god. Not that Deaton gets to treat many pets with bullet-wounds. Deaton even makes wisecracks about taking in a stray wolf, which… is in bad taste, and Stiles tells him it is, but Deaton just chuckles and pats Stiles’s head.

“He’ll be okay, kid,” the doctor says, and shuffles out. “We’ll look after him.”

Stiles wonders why Deaton doesn’t panic about having freaking _Derek Hale_ in his establishment, but then, he’s Deaton. Stiles isn’t sure the man’s physiologically capable of fear. He just helps whoever needs his help, no matter the price, no matter the risk. He’s always been that way. If Stiles’s dad had lived, they’d have gotten along great.

If - 

No.

Stiles doesn’t think like that, anymore. That way lies hell. Torment surer than anything the Bible threatens.

*

Stiles carries on. He always does. Scott pokes his head in to gawk at Derek, every now and then, like children gawk at caged tigers. Stiles shoos him away.

And when Derek wakes up, Stiles drops by to visit him in-between shifts of selling papers. Nobody seems to have linked Stiles with Derek, since nobody follows him home. It must’ve been too dark the night Derek got shot, and most people seem to have assumed that it was someone from Derek’s own organization that took him away.

The Italians are on the prowl.

It’s obvious that they’re on the prowl, but the Irish are uncharacteristically quiet, the wrong (right?) sort of quiet, like the calm before a storm.

Derek repeatedly mentions getting in contact with his uncle and getting back ‘on the job,’ but Stiles just jabs him with one of Dr. Deaton’s morphine needles when he does, and Derek’s out again, like a light.

“That stuff costs money, you know,” Deaton remarks, mildly, restocking his shelves. It isn’t exactly a complaint.

But they can’t keep Derek unconscious forever, and one afternoon, Derek surges up out of the bed like Moby Dick from the sea, unstoppable and muscles bunching under what’s left of his bandages. The Celtic tattoo between Derek’s shoulder-blades ripples, like a flame.

“No. More,” he grinds out, when Stiles high-tails it for the needle-rack, and Stiles… stops.

Derek _is_ well enough.

There’s no excuse to keep him here, like some -

“Fine,” says Stiles, and, whoa, okay, _now_ his voice is shaky. Damn it. “Fine, just - go and get yourself killed, then, see if I care. Because I don’t, by the way. I don’t care at all.”

“Stiles.”

Derek’s standing up. Walking toward him. Bare-chested and radiating the kind of warmth that would keep anyone toasty at night, but not Stiles, of course, that’s not -

“I’ll be fine.”

“Uh. You just got shot? In case you’ve forgotten - ”

Derek kisses him. Presses him against the wall and _kisses_ him, deep and hot and shudderingly good, stubble rasping and burning against Stiles’s mouth, tongue slick and teeth feral, biting Stiles’s lips and then his jaw, his ear, his throat.

Stiles’s hips jerk, and he groans. This is a bad idea. There are tons and tons of reasons this is a bad idea -

He can’t seem to _remember_ any of them -

His hands are on Derek’s shoulders, sliding over the bandages, starched cotton against his palms -

And he’s gasping, shifting, legs moving up to wrap around -

But Derek pulls away.

Stiles whines, and then stuffs his fist into his mouth, appalled, wide-eyed and breathing hard enough that he might as well have run a marathon. His entire body feels flushed, feverish, raw. Throbbing like an exposed nerve.

“I’ll come back,” Derek promises, his eyes wild, “and do this right.”

Do. Do _what_ right?

But before Stiles can ask, Derek’s shrugged on his shirt and gone out the door.

*

Stiles doesn’t hear from him for two months.

Two. _Months_.

It hadn’t meant anything. Clearly. And it’s not like Stiles is worried, or that he snaps at anyone who tries to talk to him, or that he scans the papers desperately for any news, or that he hangs around outside the hotel, waiting to catch a glimpse of those familiar dark-coated shoulders, that swaggering stride, that tilted hat.

Two months, and nothing happens.

And then, suddenly, there’s a flurry of activity. The papers burst with gory tales from the other side of town. Peter Hale, so long the bastion of the Irish mob, determined to continue it even unto the apocalypse, has been killed. No one knows who by, but it must be the Italians. The Italians deny it. Nobody believes them. They get raided in a series of uncannily accurate raids, the police loaded with information from an anonymous source that later turns out to be a young Mr. Lahey, who’d long ago ‘switched sides,’ making the Italians believe he was ratting the Hales out to the Italians, while instead ratting the Italians out to the _cops_. Stiles blinks, disbelievingly, at Isaac’s photograph in crisp grey-and-black. Isaac was one of Derek’s bodyguards. Which means Derek must have sent him to the Italians - must have set the whole thing up.

The Italian mafia is summarily destroyed in Beacon Hills. Their top man is arrested, as are most of their captains. The French mafia from the neighboring city, headed by the Argents, shock everyone by allying themselves with the Hales - with Derek, specifically - despite years of enmity. Well, the French hate the Italians even more than they hate the Irish. ‘The enemy of my enemy is my friend,’ and whatnot.

With the Italians gone, Derek shocks everyone, once more, by disbanding his group. He says that he’s turning it into a legitimate business, the supply and demand of foodstuffs, this time, not prohibited alcohol. Nor any of the other evil things. Nothing that involves killing.

Again, nobody believes him.

But Stiles does.

He _does_.

He shouldn’t. But he does, and on his eighteenth birthday, he gets a letter, an offer to work in a factory not owned by the Hales but distantly affiliated with them. Apparently, someone’s been saying nice things about Stiles. How he’s hard-working, how he’s clever, and how he deserves a break.

Stiles takes the job.

He doesn’t have much of a choice, at this point, if he still wants to feed himself and pay for his own rent outside of the orphanage. He manages to get Scott a job there, as well, lifting things and hurling sacks onto the backs of trucks, while Stiles gets recruited for office-work, tallying numbers and making sure they add up.

It’s - it’s not a life he could’ve hoped to live, just a few months ago.

It’s not a life he could’ve _ever_ lived. Not without Derek Hale.

And still, Derek doesn’t come to see him. Stiles is just complaining about that to Scott, as usual, when Scott rolls his eyes and pushes a pint of beer toward Stiles.

“Maybe he thinks you’ll feel you owe him, or whatever,” Scott shrugs. “If he’s a right sort, like you say he is, then that’d bother him. He wouldn’t want to force himself on you, y’know? Impose himself. It’d be weird.”

…oh.

 _Oh_.

“Scott, you’re a _genius_ ,” Stiles breathes, and Scott’s so stunned at anyone praising his intelligence that he just sits there, dumbfounded, as Stiles leaps from his chair and races out of the pub. Stiles runs full-tilt down the street, and down _another_ street, and another, until he’s at the offices of Hale Enterprises. The entrance to the building is guarded, naturally. Stiles brakes so hard, he almost trips.

“I’m here to see Mr. Hale,” he wheezes, almost doubled-over, and the guards - Isaac and Boyd, dressed in identical black outfits - exchange glances.

Isaac sneers, in a way that manages to be both terrifying and knowing, and stands aside. “Took you long enough, newsboy,” he says, and practically shoves Stiles in the door.

Stiles barely avoids falling flat on his face. He straightens his work-clothes, looking around the gleaming, chandelier-lit interior, hoping he doesn’t look as sweaty and filthy as he feels.

“Um,” he says to the receptionist. “I’m - ”

“Oh, it’s you, sir!” She jumps up and actually _shakes his hand_ , what the hell? “We’ve been waiting for you!”

“Y-you have?”

But before he can get an explanation, he’s being ushered down a hallway and past another door, and then there’s a massive mahogany desk and a man in a dark suit sitting _behind_ that desk, blue-eyed and sour-faced as always, and -

“Stiles,” says that rough, familiar voice, and Stiles feels his heart seize. “Hello.”

 _Hello?_  After all this time, that’s what he -

“Hi,” Stiles answers, because he’s a moron, too.

The door closes behind him, but all he can do is stand there, grinning like a fool, watching the edges of that beloved mouth twitch in return.

“You’re an ass,” Stiles blurts, when Derek finally gets up and comes around his desk.

“Hm. Yes,” Derek agrees, “but you think I’m a fine one.”

“Wha - did you just - you can _joke_? Why did you never tell me you could - ”

And then, Derek’s kissing him again, and all the ill-fitting corners of the world settle back into place, the jaggedness turning gentle, the wrongness turning right, and who cares about whether Derek can joke, anyway?

He sure as hell can kiss.

 

* * *

**fin.**

**Author's Note:**

> Like my writing? Check out [my blog](http://saucefactory.tumblr.com/)!


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